4-Nitrobenzyl carbamateCAS# 32339-07-4 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 32339-07-4 | SDF | Download SDF |
| PubChem ID | 787687 | Appearance | Powder |
| Formula | C8H8N2O4 | M.Wt | 196.2 |
| Type of Compound | Miscellaneous | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (4-nitrophenyl)methyl carbamate | ||
| SMILES | C1=CC(=CC=C1COC(=O)N)[N+](=O)[O-] | ||
| Standard InChIKey | FPBOSUGVPBRYCA-UHFFFAOYSA-N | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 4-Nitrobenzyl carbamate -protected aziridines undergo regioselective ring opening to produce β-substituted tryptamines for a series of indoles. |
| In vitro | Structure-activity relationships for 4-nitrobenzyl carbamates of 5-aminobenz[e]indoline minor groove alkylating agents as prodrugs for GDEPT in conjunction with E. coli nitroreductase.[Pubmed: 12773049]J Med Chem. 2003 Jun 5;46(12):2456-66.
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| Structure Identification | Tetrahedron. 2016 Jun 30;72(26):3802-3807.Synthesis of β-substituted tryptamines by regioselective ring opening of aziridines.[Pubmed: 27378819 ]
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4-Nitrobenzyl carbamate Dilution Calculator
4-Nitrobenzyl carbamate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 5.0968 mL | 25.4842 mL | 50.9684 mL | 101.9368 mL | 127.421 mL |
| 5 mM | 1.0194 mL | 5.0968 mL | 10.1937 mL | 20.3874 mL | 25.4842 mL |
| 10 mM | 0.5097 mL | 2.5484 mL | 5.0968 mL | 10.1937 mL | 12.7421 mL |
| 50 mM | 0.1019 mL | 0.5097 mL | 1.0194 mL | 2.0387 mL | 2.5484 mL |
| 100 mM | 0.051 mL | 0.2548 mL | 0.5097 mL | 1.0194 mL | 1.2742 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Synthesis of beta-substituted tryptamines by regioselective ring opening of aziridines.[Pubmed:27378819]
Tetrahedron. 2016 Jun 30;72(26):3802-3807.
Functionalized tryptamines are targets of interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis if site selectivity can be controlled. 4-Nitrobenzyl carbamate (PNZ)-protected aziridines undergo regioselective ring opening to produce beta-substituted tryptamines for a series of indoles. The PNZ-protected tryptamines can be further manipulated by PNZ removal under mild conditions.
Structure-activity relationships for 4-nitrobenzyl carbamates of 5-aminobenz[e]indoline minor groove alkylating agents as prodrugs for GDEPT in conjunction with E. coli nitroreductase.[Pubmed:12773049]
J Med Chem. 2003 Jun 5;46(12):2456-66.
Twelve substituted 4-Nitrobenzyl carbamate prodrugs of the 5-aminobenz[e]indoline class of DNA minor groove alkylating agents were prepared and tested as prodrugs for gene-directed enzyme prodrug therapy (GDEPT) using a two-electron nitroreductase (NTR) from E. coli B. The prodrugs and effectors were tested in a cell line panel comprising parental and transfected human (SKOV/Skov-NTR(neo), WiDr/WiDr-NTR(neo)), Chinese hamster (V79(puro)/V79-NTR(puro)), and murine (EMT6/EMT6-NTR(puro)) cell line pairs. In the human cell line pairs, several analogues bearing neutral methoxyethoxy-, 2-hydroxyethoxy-, or 3-hydroxypropoxy-substituted side chains were good substrates for NTR as measured by cytotoxicity ratios, with NTR-ve/NTR+ve ratios similar to the established NTR substrates CB1954 (an aziridinyl dinitrobenzamide) and the analogous bromomustard. Selectivity for NTR decreased with increasing side-chain size or the presence of a basic amine group. Low to modest selectivity was observed in the Chinese hamster-derived cell line pair; however, in the murine EMT6/EMT6-NTR(puro) cell line pair, the above hydroxyalkoxy analogues again showed significant selectivity for NTR. The activity of the 2-hydroxyethoxy analogue was evaluated against NTR-expressing EMT6 tumors comprising ca. 10% NTR+ve cells at the time of tumor treatment. A small decrease in NTR+ve cells was observed after treatment, with a lesser effect against NTR-ve target cells, but these effects were not statistically significant and were much less than for the dinitrobenzamides. These results suggest that useful GDEPT prodrugs based on the 4-Nitrobenzyl carbamate and 5-aminobenz[e]indoline motifs may be developed if optimization of pharmacokinetics can be addressed.
